Well actually I think Fyodor has been in Japan for a while.

During Dead Apple Fyodor was

there watching Chuuya and Dazai confront Shibusawa from afar. And I think during then they
were about 16-17? Because that happened 6 years ago from the current timeline. Fyodor was
definitely in Japan during that time doing whatever the fuck

My theory is that Dazai at some point caught Fyodor’s eye while he was still in the mafia,
and once Dazai left, Fyodor was able to make contact with him and most likely tried to
recruit him onto his side (not sure if the DOA existed at that point or if it was just Fyodor on
his own). But Dazai vowed to live his life to help others as he promised to Oda so he refused.
I mean think about it, young Dazai really could be a perfect partner for Fyodor with his
history of horrible crimes and his ability and their shared intelligence. But it’s because of
Oda’s death that changed Dazai. I also imagine Dazai wouldn’t be the biggest fan of Fyodor
who has a habit of strapping explosives to small children

Tho this is just my theory we won’t have any idea what happened between them until Asagiri
tells us but its fun fanfic fuel I guess